This invention relates to diamines which are suitable for use as urethane catalysts. The invention also relates to a method of making these compounds and to their use as catalysts and/or antimicrobial agents. The invention further relates to an intermediate compound which is used in the preparation of these catalysts. The invention also relates to a method of using such intermediates as antimicrobial agents.
Several spiro compounds are well-known and their preparation is mentioned in work by, for instance, Movsumzade et al., Azerbaidzhanskii Khimicheskii Zhurnal, vol. 3, pp. 53-8 and others.
The production of di-(N,N'-disubstituted amino) alkanes and their use as polyurethane catalysts, epoxy curing agents and as intermediates in the preparation of corrosion inhibitors, pharmaceuticals, emulsifiers, textile chemicals, rubber chemicals and the like are also generally well known. U.S. Pat. No. 4,103,087 teaches that di-(N,N'-disubstituted amino) alkanes may be prepared with high selectivity by use of a heterogeneous alumina phosphate catalyst. Prior art polyurethane catalysts include 2,2'-dimorpholinodiethylether (DMDEE).
The work cited in the prior art provides methods for preparing certain symmetrical diamines, but provides no suitable method for preparing unsymmetrical diamines.